Ethanol → 5-[N-(3',5'-Bistrifluoromethylbenzyl)amino]-2-methyltetrazole

HRID 390739

반응식

HRID 390739 반응식
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH:6]=O.[CH3:17][N:18]1[N:22]=[N:21][C:20]([NH2:23])=[N:19]1.C(O)C.[BH4-].[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH2:6][NH:23][C:20]1[N:21]=[N:22][N:18]([CH3:17])[N:19]=1

참가 물질

6

반응물 4

HCID 702EthanolHCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 1386772-methyl-2H-1,2,3,4-tetrazol-5-amineHCID 4311764Sodium borohydride

생성물 1

HCID 230732215-[N-(3',5'-Bistrifluoromethylbenzyl)amino]-2-methyltetrazole수율 87.6%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 3,5-bis(trifluoromethyl)benzaldehyde (4 g, 16.5 mmol), 2-methyl-2H-tetrazol-5-amine (1.96 g, 19.8 mmol) and molecular sieves (5-10 Å beads) in toluene (50 mL) was heated at reflux for 4 hours, after which time the solvent was removed. Ethanol (50 mL) and sodium borohydride (1.25 g, 33 mmol) were added. The resulting mixture was stirred at room temperature for 30 minutes and then partitioned between saturated NH4Cl (50 mL) and ethyl acetate (2×50 mL). The combined organic layers were washed with saturated NaCl (50 mL), dried (MgSO4), filtered and concentrated to yield the title compound as a white solid (4.7 g). 1H NMR (400 MHz, CDCl3) δ 4.2 (s, 3 H) 4.7 (s, 1 H) 4.7 (s, 1 H) 5.0 (t, J=6.0 Hz, 1 H) 7.8 (s, 1 H) 7.9 (s, 2 H). MS (ES+) Calc: 325.08, Found: 325.8 (M+1).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customafter which time the solvent was removed
  4. custompartitioned between saturated NH4Cl (50 mL) and ethyl acetate (2×50 mL)
  5. washThe combined organic layers were washed with saturated NaCl (50 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-63ad3bc616ff479fa3780317a102f092
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383660B2

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